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Oxidation of Alcohols

  • Page ID
    21334
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    ​Chromium based oxidations

    Cr-Overview.png

    Typical Oxidants:

    Chromium oxidants in aqueous media will oxidize primary alcohols to the corresponding carboxylic acid. The use of PCC, PDC, and Collins Reagent in methylene chloride allows for selective oxidation to the aldehyde.

    Tertiary, vinylic alcohols are known to undergo 3,3-sigmatropic rearrangements.

    Cr-3,3.png

    DMSO based oxidations

    DMSO-overview.png

    Swern Oxidation

    DMSO-Swern.png

    IBX/DMP

    IBX:DMP prep.png

    IBX can be used to oxidize 1,2-diols without C–C bond cleavage.

    IBX-1,2-diols.png

    Tetrahedron Lett., 1994, 35, 8019-8022.

    Selective Oxidations

    1° Selective

    TEMPO

    Tempo can be used to oxidize primary alcohols to aldehydes.

    TEMPO.png

    Tetrahedron Lett., 1992, 33, 5029-5033.

    TEMPO-mech.png

    TEMPO can be used to selectively oxidize primary alcohols in the presence of secondary alcohols.

    TEMPO-selectivity.png

    Org. Lett., 2004, 6, 3985-3988.

    2° Selective

    Fetizen's Reagent: Ag2CO3 on celite

    Fetizen-1.png

    Fetizen-2.png

    Ceric ammonium Nitran (CAN)

    CAN.png

    NaOCl (Bleach)

    Bleach.png

    Triphenylcarbenium tetrafluoroborate (TrBF4)

    TrBF4.png

    Allylic/Benzylic Selective

    MnO2.png


    Oxidation of Alcohols is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.

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